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. 2018 Oct 2;9(48):9012–9017. doi: 10.1039/c8sc03493a

Table 1. Optimization of reaction conditions a .

Inline graphic
Entry Variations from the standard conditions Yield b
1 None 83%
2 w/o HE 0% c
3 Dark 0%
4 Dark, 80 °C 0% c
5 w/o DABCO 22% c
6 TMEDA, instead of DABCO 43%
7 DBU, instead of DABCO 19%
8 Et3N, instead of DABCO 26%
9 Pyridine, instead of DABCO 19%
10 Cs2CO3, instead of DABCO 21%
11 6, instead of HE 25%
12 7, instead of 4 19%
13 8, instead of 4 25%
graphic file with name c8sc03493a-u2.jpg

aReaction conditions: styrene 2 (0.1 mmol), 4-cyanopyridine 3 (2.0 equiv.), Togni reagent 4 (1.5 equiv.), Hantzsch ester (HE, 1.5 equiv.), DABCO (1.5 equiv.), MTBE [0.05 M], 90 W blue LED, and rt.

bYields were determined by 19F NMR using an internal standard.

cMajor byproducts determined were dimers of benzylic radicals; see the ESI for details. DABCO: 1,4-diazabicyclo[2.2.2]octane; MTBE: methyl tert-butyl ether.